Methyl iodide → 4-Iodo-2-methoxybenzyl alcohol

HRID 1421696

반응식

HRID 1421696 반응식
[OH:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[C:11]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C>[CH3:11][O:1][C:2]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 187797342-(Hydroxymethyl)-5-iodophenol

생성물 1

HCID 187797924-Iodo-2-methoxybenzyl alcohol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Hydroxy-4-iodo-benzylalcohol from Step 3 (1.0 g, 4.0 mmol), Cs2CO3 (1.3 g, 4.0 mmol) and iodomethane (0.25 mL, 4.0 mmol) were dissolved in DMF and heated to 80° for 1 hour and then stirred at room temperature for 2 hours. The DMF was removed in vacuo and the residue was partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc (2×). The organic layers were combined, washed with H2O and brine, dried (MgSO4), filtered and concentrated to yield an oil. This oil was purified by flash chromatography eluting product with 30% EtOAC/Hexane to give the title compound.

후처리

  1. temperatureheated to 80° for 1 hour
  2. customThe DMF was removed in vacuo
  3. customthe residue was partitioned between H2O and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc (2×)
  5. washwashed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield an oil
  10. customThis oil was purified by flash chromatography
  11. washeluting product with 30% EtOAC/Hexane

출처 및 근거

ORD 기록
ord-b83e0f681e2748e286146465b4abbc59
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077853

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